Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 38, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202207486
Keywords
Annulenes; Aromaticity; Nanocarbons; Redox Chemistry; Structure Elucidation
Categories
Funding
- Polish German BEETHOVEN CLASSIC program - National Science Center of Poland [UMO-2018/31/G/ST5/01813]
- Polish German BEETHOVEN CLASSIC program - German Science Foundation (DFG) [VO 829/14-1]
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Tridecacyclene tetraimide (TCTI), an electron-deficient non-benzenoid nanocarbon, was synthesized with a concise method. TCTI has a non-planar structure and forms pi-stacked dimers in the solid state. In solution, it undergoes eight single-electron reductions, resulting in a range of negatively charged states. The TCTI anions exhibit extended near-infrared absorptions, with a strong band at 1692 nm for the dianion. Computational analysis indicates that the stability of TCTI anions is attributed to the electron-deficient imide groups and the local aromaticity of the reduced acenaphthylene units. TCTI shows potential applications in electrochromic and charge storage fields.
Tridecacyclene tetraimide, TCTI, an electron-deficient non-benzenoid nanocarbon with a C56N4 polycyclic framework was obtained in a concise synthesis. TCTI has a non-planar structure and forms pi-stacked dimers in the solid state. In solution, it undergoes eight single-electron reductions, yielding a range of negatively charged states up to an octaanion. Except for the latter species, which has a remarkably large electronic gap, the anions feature extended near-infrared absorptions, with a particularly strong band at 1692 nm observed for the dianion. A computational analysis of the TCTI anions shows that their stability originates from the combined effects of electron-deficient imide groups and the local aromaticity of reduced acenaphthylene units. The properties of TCTI make it potentially useful in electrochromic and charge storage applications.
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